JP3672574B2 - 薬剤の結晶変形 - Google Patents
薬剤の結晶変形 Download PDFInfo
- Publication number
- JP3672574B2 JP3672574B2 JP53628898A JP53628898A JP3672574B2 JP 3672574 B2 JP3672574 B2 JP 3672574B2 JP 53628898 A JP53628898 A JP 53628898A JP 53628898 A JP53628898 A JP 53628898A JP 3672574 B2 JP3672574 B2 JP 3672574B2
- Authority
- JP
- Japan
- Prior art keywords
- weak
- deformation
- crystal
- difluorobenzyl
- triazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000013078 crystal Substances 0.000 title claims description 26
- 239000003814 drug Substances 0.000 title description 4
- 229940079593 drug Drugs 0.000 title 1
- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 13
- 238000001237 Raman spectrum Methods 0.000 claims description 11
- 238000012986 modification Methods 0.000 claims description 11
- 230000004048 modification Effects 0.000 claims description 11
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000009102 absorption Effects 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 238000010586 diagram Methods 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000001028 reflection method Methods 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- BOWZTNKTHNKHQH-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]triazole Chemical compound FC1=CC=CC(F)=C1CN1N=NC=C1 BOWZTNKTHNKHQH-UHFFFAOYSA-N 0.000 description 1
- PVIAOIJYIQHKPL-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]triazole-4-carbonitrile Chemical compound FC1=CC=CC(F)=C1CN1N=NC(C#N)=C1 PVIAOIJYIQHKPL-UHFFFAOYSA-N 0.000 description 1
- OPJHWTKDQYKYHL-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1=C(F)C=CC=C1F OPJHWTKDQYKYHL-UHFFFAOYSA-N 0.000 description 1
- JSZUBPHMRHROHZ-UHFFFAOYSA-N 2-(azidomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CN=[N+]=[N-] JSZUBPHMRHROHZ-UHFFFAOYSA-N 0.000 description 1
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 description 1
- -1 4-cyano-1- (2,6-difluorobenzyl) -1H-1,2,3-triazole 2,6-difluorobenzyl azide Chemical compound 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH140497 | 1997-06-10 | ||
CH1404/97 | 1997-06-10 | ||
PCT/EP1998/003427 WO1998056772A1 (en) | 1997-06-10 | 1998-06-08 | Crystal modification of 1-(2,6-difluorobenzyl)-1h-1,2,3--triazole-4-carboxamide and its use as antiepileptic |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2000516258A JP2000516258A (ja) | 2000-12-05 |
JP3672574B2 true JP3672574B2 (ja) | 2005-07-20 |
Family
ID=4209650
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53628898A Expired - Lifetime JP3672574B2 (ja) | 1997-06-10 | 1998-06-08 | 薬剤の結晶変形 |
JP53628998A Expired - Lifetime JP3672575B2 (ja) | 1997-06-10 | 1998-06-08 | 薬剤の結晶変形 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53628998A Expired - Lifetime JP3672575B2 (ja) | 1997-06-10 | 1998-06-08 | 薬剤の結晶変形 |
Country Status (36)
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW526195B (en) | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
TW200404802A (en) * | 2002-05-31 | 2004-04-01 | Schering Corp | Xanthine phosphodiesterase V inhibitor polymorphs |
GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
US7875284B2 (en) * | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
US20090069390A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched rufinamide |
CA2736703A1 (en) | 2008-10-13 | 2010-04-22 | Cipla Limited | Process for the preparation of rufinamide |
CN101768124B (zh) * | 2008-12-30 | 2012-01-04 | 北京本草天源药物研究院 | 一种药物晶体及其制备方法和用途 |
IT1395736B1 (it) * | 2009-08-04 | 2012-10-19 | Dipharma Francis Srl | Forme cristalline di rufinamide |
JP2013503861A (ja) * | 2009-09-04 | 2013-02-04 | タクティカル セラピューティクス インコーポレイテッド | 新規の組成物、ならびに5−アミノまたは置換アミノ1,2,3−トリアゾールおよびトリアゾールオロチン酸塩製剤を調製する方法 |
EP2563766B1 (en) | 2010-04-30 | 2014-06-25 | Laboratorios Lesvi, S.L. | Improved process for preparing rufinamide intermediate |
EP2465853A1 (en) | 2010-12-14 | 2012-06-20 | Laboratorios Lesvi, S.L. | Polymorph of rufinamide and process for obtaining it |
ITMI20110718A1 (it) | 2011-04-29 | 2012-10-30 | Dipharma Francis Srl | Procedimento per la purificazione di rufinamide |
US10206874B2 (en) | 2012-07-20 | 2019-02-19 | Hetero Research Foundation | Rufinamide solid dispersion |
WO2021099481A1 (en) | 2019-11-20 | 2021-05-27 | Medichem, S.A. | Solid composition containing rufinamide |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3992378A (en) | 1973-12-26 | 1976-11-16 | Eli Lilly And Company | Fluoralkyl quinoxadinediones |
US4156734A (en) | 1976-02-13 | 1979-05-29 | Merck & Co., Inc. | Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid |
GB1511195A (en) | 1976-10-18 | 1978-05-17 | Ici America Inc | Triazole derivatives |
US4536518A (en) | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
US4346097A (en) * | 1980-09-30 | 1982-08-24 | Warner-Lambert Company | Method for treating convulsions with pyrazole-4-carboxamide derivatives |
US4789680A (en) * | 1982-12-23 | 1988-12-06 | Ciba-Geigy Corporation | Aralkyltriazole compounds |
FI834666A7 (fi) | 1982-12-23 | 1984-06-24 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya aralkyltriazolfoereningar. |
US4511572A (en) * | 1983-03-18 | 1985-04-16 | The University Of Kentucky Research Foundation | Triazoline anticonvulsant drugs |
PH22568A (en) * | 1985-04-18 | 1988-10-17 | Ciba Geigy Ag | Fluorinated benzyl triazoles and pharmaceutical compositions containing the same |
CA2002864C (en) | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
JPH02214504A (ja) | 1989-02-15 | 1990-08-27 | Nissan Chem Ind Ltd | 光学活性キノキサリン化合物の晶析法 |
WO1991001724A1 (en) | 1989-07-27 | 1991-02-21 | G.D. Searle & Co. | Renal-selective prodrugs for the treatment of hypertension |
IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
CA2095444C (en) | 1990-11-06 | 2001-06-19 | Shuichi Sakamoto | Fused pyrazine derivatives |
JP2753911B2 (ja) | 1991-12-06 | 1998-05-20 | キッセイ薬品工業株式会社 | N−tert−ブチル−1−メチル−3,3−ジフェニルプロピルアミン塩酸塩の結晶多形およびその製造方法 |
DE4217952A1 (de) | 1992-05-30 | 1993-12-02 | Basf Ag | Chinoxalin-2,3(1H,4H)-dione |
US5248699A (en) | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
US5631373A (en) | 1993-11-05 | 1997-05-20 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon | Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones |
GB9418443D0 (en) | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
GB9419318D0 (en) | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
CA2213693C (en) | 1995-02-22 | 2008-04-15 | Hoechst Pharmaceuticals & Chemicals K.K. | Amorphous piretanide, piretanide polymorphs, process for their preparation and their use |
HU226425B1 (en) * | 1996-07-11 | 2008-12-29 | Novartis Ag | Process for preparing 1-substituted 4-cyano-1,2,3-triazoles |
TW526195B (en) * | 1997-06-10 | 2003-04-01 | Novartis Ag | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
-
1998
- 1998-06-04 TW TW087108858A patent/TW526195B/zh not_active IP Right Cessation
- 1998-06-04 TW TW087108859A patent/TW403740B/zh not_active IP Right Cessation
- 1998-06-08 TR TR1998/01630T patent/TR199801630T1/xx unknown
- 1998-06-08 CA CA002256013A patent/CA2256013C/en not_active Expired - Lifetime
- 1998-06-08 KR KR10-1998-0708150A patent/KR100425656B1/ko not_active Expired - Lifetime
- 1998-06-08 AT AT98934929T patent/ATE232852T1/de active
- 1998-06-08 ID IDW980065D patent/ID27660A/id unknown
- 1998-06-08 PE PE1998000479A patent/PE80999A1/es not_active IP Right Cessation
- 1998-06-08 RU RU99104299/04A patent/RU2194041C2/ru active
- 1998-06-08 CZ CZ19982534A patent/CZ292260B6/cs not_active IP Right Cessation
- 1998-06-08 WO PCT/EP1998/003427 patent/WO1998056772A1/en active IP Right Grant
- 1998-06-08 PE PE1998000478A patent/PE79799A1/es not_active IP Right Cessation
- 1998-06-08 TR TR1998/01631T patent/TR199801631T1/xx unknown
- 1998-06-08 HU HU0000798A patent/HU226107B1/hu unknown
- 1998-06-08 SI SI9830405T patent/SI0994863T1/xx unknown
- 1998-06-08 CA CA002256015A patent/CA2256015C/en not_active Expired - Lifetime
- 1998-06-08 ES ES98934929T patent/ES2192779T3/es not_active Expired - Lifetime
- 1998-06-08 JP JP53628898A patent/JP3672574B2/ja not_active Expired - Lifetime
- 1998-06-08 PT PT98934930T patent/PT994864E/pt unknown
- 1998-06-08 DE DE69813560T patent/DE69813560T2/de not_active Expired - Lifetime
- 1998-06-08 SK SK1094-98A patent/SK283734B6/sk not_active IP Right Cessation
- 1998-06-08 DK DK98934929T patent/DK0994863T3/da active
- 1998-06-08 DE DE122007000051C patent/DE122007000051I2/de active Active
- 1998-06-08 CN CN988000113A patent/CN1132820C/zh not_active Expired - Lifetime
- 1998-06-08 CN CNB988056755A patent/CN1159300C/zh not_active Expired - Lifetime
- 1998-06-08 SI SI9830450T patent/SI0994864T1/xx unknown
- 1998-06-08 PL PL330764A patent/PL191943B1/pl unknown
- 1998-06-08 ES ES98934930T patent/ES2197485T3/es not_active Expired - Lifetime
- 1998-06-08 DE DE69811500T patent/DE69811500T2/de not_active Expired - Lifetime
- 1998-06-08 WO PCT/EP1998/003428 patent/WO1998056773A1/en active IP Right Grant
- 1998-06-08 SK SK1093-98A patent/SK283685B6/sk not_active IP Right Cessation
- 1998-06-08 NZ NZ331370A patent/NZ331370A/xx not_active IP Right Cessation
- 1998-06-08 US US09/125,329 patent/US6740669B1/en not_active Expired - Lifetime
- 1998-06-08 NZ NZ331371A patent/NZ331371A/xx not_active IP Right Cessation
- 1998-06-08 AU AU84372/98A patent/AU725517B2/en not_active Expired
- 1998-06-08 CA CA2614926A patent/CA2614926C/en not_active Expired - Lifetime
- 1998-06-08 PL PL330798A patent/PL192114B1/pl unknown
- 1998-06-08 IL IL12573298A patent/IL125732A/en not_active IP Right Cessation
- 1998-06-08 KR KR10-1998-0708149A patent/KR100409168B1/ko not_active Expired - Lifetime
- 1998-06-08 BR BR9804947A patent/BR9804947A/pt not_active Application Discontinuation
- 1998-06-08 HU HU0002113A patent/HU225153B1/hu unknown
- 1998-06-08 CN CNB2004100473675A patent/CN1298708C/zh not_active Expired - Lifetime
- 1998-06-08 DK DK98934930T patent/DK0994864T3/da active
- 1998-06-08 BR BR9804946A patent/BR9804946A/pt not_active Application Discontinuation
- 1998-06-08 CZ CZ19982533A patent/CZ292481B6/cs not_active IP Right Cessation
- 1998-06-08 IL IL12573398A patent/IL125733A/en active Protection Beyond IP Right Term
- 1998-06-08 AT AT98934930T patent/ATE237599T1/de active
- 1998-06-08 EP EP98934929A patent/EP0994863B1/en not_active Expired - Lifetime
- 1998-06-08 EP EP98934930A patent/EP0994864B1/en not_active Expired - Lifetime
- 1998-06-08 ID IDW980066D patent/ID21014A/id unknown
- 1998-06-08 AU AU84371/98A patent/AU725528B2/en not_active Expired
- 1998-06-08 RU RU99104300/04A patent/RU2198167C2/ru active
- 1998-06-08 JP JP53628998A patent/JP3672575B2/ja not_active Expired - Lifetime
- 1998-06-09 AR ARP980102707A patent/AR012945A1/es not_active Application Discontinuation
- 1998-06-09 MY MYPI98002570A patent/MY120156A/en unknown
- 1998-06-09 ZA ZA984967A patent/ZA984967B/xx unknown
- 1998-06-09 CO CO98032885A patent/CO4940448A1/es unknown
- 1998-06-09 MY MYPI98002572A patent/MY125854A/en unknown
- 1998-06-09 ZA ZA984966A patent/ZA984966B/xx unknown
- 1998-06-09 AR ARP980102708A patent/AR012946A1/es not_active Application Discontinuation
- 1998-06-09 CO CO98032879A patent/CO4940452A1/es unknown
- 1998-08-11 NO NO19983666A patent/NO329314B1/no not_active IP Right Cessation
- 1998-08-11 NO NO19983667A patent/NO329315B1/no not_active IP Right Cessation
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1999
- 1999-12-10 UY UY25844A patent/UY25844A1/es not_active Application Discontinuation
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2001
- 2001-05-31 US US09/871,366 patent/US6455556B2/en not_active Expired - Lifetime
-
2002
- 2002-11-14 US US10/294,408 patent/US20030125568A1/en not_active Abandoned
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2004
- 2004-02-26 US US10/787,528 patent/US20040167186A1/en not_active Abandoned
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2006
- 2006-01-11 US US11/329,945 patent/US7750028B2/en not_active Expired - Fee Related
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2007
- 2007-05-17 AR ARP070102131A patent/AR061004A2/es unknown
- 2007-05-17 AR ARP070102132A patent/AR061005A2/es not_active Application Discontinuation
- 2007-07-03 NL NL300284C patent/NL300284I2/nl unknown
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